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Dimethylformamide → 2-Bromo-1-(3-methylbut-2-enylthio)benzene

HRID 22991
Notes
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Reaction equation

HRID 22991 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].CN(C=O)C.C(=O)([O-])[O-].[K+].[K+].Br[CH2:21][CH:22]=[C:23]([CH3:25])[CH3:24]>O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][CH2:21][CH:22]=[C:23]([CH3:25])[CH3:24]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 700922-Butene, 1-bromo-3-methyl-HCID 805982-Bromobenzenethiol

Product 1

HCID 106348752-Bromo-1-(3-methylbut-2-enylthio)benzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

19.30 g (102.0 mmol) of 2-bromothiophenol, 160 ml of DMF and 15.50 g (112.0 mmol) of potassium carbonate are introduced into a three-necked flask. 13 ml (112.0 mmol) of 1-bromo-3-methyl-2-butene are added dropwise and the reaction mixture is stirred at room temperature for two hours. It is poured into water and extracted with ethyl acetate and the organic phase is separated by settling, washed with water, dried over magnesium sulphate and evaporated. 26.00 g (99%) of the expected compound are collected in the form of an orangey oil.

Workup

  1. extractionextracted with ethyl acetate
  2. customthe organic phase is separated
  3. washwashed with water
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. custom26.00 g (99%) of the expected compound are collected in the form of an orangey oil

Sources & evidence

ORD record
ord-cc4dd4a925134e97806965f18a207e98
Source dataset
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06849658B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes